Episode 38 – Alli Webb, Founder of Drybar

This week kicks off a special series of shows we’re calling our “Starter Series.” Each week we’ll hear from someone who knows what it takes to go from a moment of inspiration to a realized dream. To start us off, Jessica chats with Alli Webb. Alli is the founder of Drybar, a business that started as an outlet for a stay-at-home mom and has now become a $100 million dollar brand!

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Jessica: Hey there, it’s Jessica Honegger, Founder of the socially conscious fashion brand Noonday Collection. And this is The Going Scared Podcast where we cover all things impact, entrepreneurship, and courage. This week begins a brand-new series of shows where we dig into what it looks like to begin, to start, to make it happen. In this upcoming series, we’re going to be talking with fitness gurus, entrepreneurs, non-profit founders, and we’re even going to talk about how your Enneagram number interacts with this whole idea of starting.

I love the quote by Rumi that says, "If you start to walk on the way, the way appears." Maybe it’s a goal in your life, a business, a nudge that you lay down after the kids came, whatever it is, we are going to be spending time with people who’ve taken big leaps so that we can go and do likewise. And our very first guest on this series is the one and only Alli Webb, founder of the Drybar.

I got my first blowout from the Drybar a few years ago and learned more about Alli’s story from this year’s Inc. Magazine‘s issue, "How I Did It," where Alli was the cover girl. And I was actually one of the featured entrepreneurs right along with her, which was super humbling.

So, in 2008, Alli began a side business called, Straight at Home, which provided in-home blowouts on a referral basis in L.A. And when her business and popularity grew, she decided to expand, and start, and open her very first Drybar. They now have 100 plus locations throughout the U.S. and Canada. And they have a growing product line that is created specifically for the perfect blowout. It’s sold through Drybar as well as Sephora, Nordstrom, Ulta, and more.

And in 2014, she received the CEW Achiever Award. She’s made it to Fortune‘s 40 Under 40 list, Marie Claire‘s “16 Most Fascinating Women,” Cosmopolitan‘s “2013 Power List.” As you can see, Alli is certainly a starter, but what she started has actually changed the way women think about hair, beauty, and even themselves. And so that’s why I’m so excited for you to hear the conversation that I got to have with her.

I want to hear the story behind the story of the Drybar before… Of course, I’m going to ask you the origin story because we just all love a good origin story. But tell me a little bit more about the story behind the story?


From Straight at Home to the Drybar

Alli: I really struggled with my hair, and I don’t know why it was so important to me, but when I was growing up in South Florida, you know, where it’s, like, very humid outside, so, if you have any kind of curl or wave in your hair, or you’re prone to any kind of frizz, I mean, you’re basically going out into moisture-rich air.

Jessica: It’s misery.

Alli: And so my hair was just always so crazy, and I just…it was, like, unruly, and I felt like it just didn’t look good or it didn’t look like pretty, and polished, and presentable, and all that stuff. And this is like when I’m a really little kid, I mean, 9, 10 years old. And I used to beg my mom to blowout my hair who was not a professional hairstylist by any stretch. But I loved the way my hair looked straight. And I don’t know where that came from, but that was what I always wanted.

Jessica: Well, it came from, I mean, the images of beauty that probably were around at the time. Although I have to say this is so funny, but my husband and I this weekend were, like, "It is time that we introduced our kids to, Can’t Buy Me Love."

Alli: Yeah. So maybe…

Jessica: So, we really watched, Can’t Buy Me Love, Saturday night, Cindy and Ronnie, and we were kicking it back. And it was funny because as I was reading your book today, I was like, "Actually she was super on…" Oh, I don’t know how old you are at all, but I’m, like, for that period, like, your hair was looking good, actually. But I know at the time it was…

Alli: Well it was. I mean, that was the style. I mean, people, you know, wore, like, curly big hair and big bangs on.

Jessica: Big hair, yeah.

Alli: You know, I made the best with what I had, but I didn’t love it. And I loved, you know, to your point about society. It was, like, you know, Cindy Crawford and Christie Brinkley. I mean, they had stylists who were…

Jessica: Straight hair.

Alli: I now understand that. But they had stylists that were blowing their hair out and did this, like, you know, perfect…like, whipped perfection of bouncy, straight hair. And I was just very mystified. Like, "How in the world do they get hair like that?"

And so I was, like, it was this curiosity that was piqued in me very, very young. And fast forward to spending countless, countless hours in the bathroom in high school trying to figure out how to blow out my own hair to, you know, finally after trying a couple other careers, but finally, and one being in fashion. But trying… I decided to go to beauty school in my early 20s. And it was really, like, the best decision, obviously, I ever made.

But at that time in my life, it was a tough decision to make because my parents weren’t really…they didn’t see much of it for me, and I think they didn’t love the idea of me being in the service industry. And they didn’t love…like they didn’t think it was going to…you know, my parents also are entrepreneurs, and they had their own clothing stores.

“It was this curiosity that was piqued in me very, very young… Finally after trying a couple other careers… I decided to go to beauty school in my early 20s. And it was really, like, the best decision, obviously, I ever made. But at that time in my life, it was a tough decision to make.” Alli Webb on choosing to pursue her passion.

It was, like, little old lady clothing store. It was, like…and next to their clothing store was always, like, a little old lady hair salon. And I think my parents maybe had this vision in their mind that that’s where I wanted to work. And I was like, "No, I want to go to beauty school. I want to learn how to blow out my own stupid hair. And then I want to go to New York and do fashion shows, and editorial, and all of that."

And that was kind of, like, my little dream that I hope to do, but the other thing about it with going to beauty school was…you know, it was, like, I found my people and I really felt like that. But I felt I was around all these other people who were…also loved hair as much as I did. And it was, like, it did not feel like school. It was so fun and I had the best time. And it was one of those very fulfilling moments where I was, like, "Wow, this is really where I’m meant to be." And then I’ve been doing hair professionally, really, ever since.


Getting Started by Finding Where We Flourish

Jessica: OK. So you discovered these are my people. This is what I love. This what makes me come alive. And so you were a professional hairstylist for other people, and you did editorial in New York for a while?

Alli: I mean, I didn’t really end up ever doing that. I moved to New York City after doing hair for about five years or so in South Florida where I was living at the time, and it was, like, I couldn’t get to New York fast enough. And it was my second time actually living in New York. I also moved to New York when I was 18 before beauty school, which is a whole other story.

But I got to New York. I worked for John Sahag who was a very famous hairdresser in his right. He’s kind of the pioneer of dry cutting, and he was, like, the guy to work for. And I walked into that salon with my leather pants on, and I was like, "I’m getting this job." And I did. And it was another really fantastic experience because he was such…and most people probably listening won’t know, but if you’re a hairdresser around my age, you know who he is.

And he was just this really interesting, very soft-spoken, like, rockstar, cool guy, that just was the coolest thing ever. And anyway, I ended up working for him for a couple of years. And the way their method of cutting hair was they flat ironed the hair, like, when you come in, and make your hair super-duper straight. They cut it and then an assistant, in that case, me, would wash the hair and then blow it out.

Jessica: Oh, really? They straightened it before the wash?

Alli: Yeah. And that was kind of part of their whole technique for cutting. I really never cut hair in that salon. I was always an assistant blow-drying hair, and I did that for a long time. And I learned a lot, but I blew out just so many people. Even, like, I would blow out John’s girlfriend, and that was very pressure-filled. But it was all, you know, part of me honing that skill of blow-drying hair, and I got pretty good at it.

And anyways I worked there for a while, and then I actually jumped around and decided I didn’t want to do hair for a while, and ended up meeting my husband and moving to South Florida, had a couple of kids, and became a stay-at-home mom in Los Angeles. And it was kind of during that time I spent about five years at home with my boys.

And then after about five years of staying at home, which I thought was going to be it for me because I was so over the moon about been able to just be a stay-at-home mom, I just kind of got the itch again to do something for myself, and that’s when I started my mobile blow dry business, which is called, Straight at Home. That eventually is really what led me to Drybar because I realized during that operation that I was getting so busy and I didn’t have enough…I really didn’t have enough of me to go around. The demand was really piling up.

So, I went to my brother, who’s also bald and had no business in the hair industry, said I wanted to turn my little mobile blow dry business into a brick and mortar, instead of me going to them, they come to me. And so that is really how the whole idea got started, and that was like…we started talking about this, I’d say, like, in 2009.

Jessica: Yeah. So, tell me a little bit about these five years because you seem like a really driven person. I mean, not anyone just decides I’m going to go to New York. I’m going to work for the top hairstylist in town. I’m definitely going to get the job, and then you get married, and then it seems like…did you take some of that ambition and were you poring it into your kids? Were you like kind of a Pinterest mom, and you were making a hardcore momming it for those few years, or tell me a little bit about that?

Alli: You know, when my first son Grant was born, I was so, like, immersed in the mommy community and I loved it, and it was so fun. And Grant was, like…I took him everywhere. I was always wearing him, and it was just the greatest thing ever I did. I loved it so much. And then my second son was born. It just got a little bit harder. I was like, "Ah." I don’t know. I mean, and it was just, like, I found myself in this kind of treadmill of going to the park every day, kind of doing the exact same thing every day, and I just didn’t feel personally fulfilled.


Discovering a Need and Fulfilling It  

Of course, I adore my kids and I think… You know, my parents worked and owned their own business, and I think it’s great that my kids see how hard we work. But I just got a little, like…I felt like I didn’t have anything for myself, and I was giving everything I had to my kids and my family, which was amazing and very admirable, and anybody who decides to be a stay-at-home mom, like, I think that’s an amazing choice.

It’s just after five years, for me, I just felt like I needed to do something for myself, and I didn’t expect that. Like I said, I was expecting to be just, like, honed in on this and I was thinking I wanted to maybe have more than two kids. But it just, you know, something shifted in me, and I decided I wanted to start to do something for myself.

And the mobile business was a great way to get back out there slowly because I was able to make my own hours. I could say yes or no. I didn’t have to answer to anybody. And so it was really perfect for the time. And again, at the time, I thought, like, that would be enough. And then I couldn’t help feeling like there is this massive hole in the market for a place like Drybar.

And I mean I really felt, like, it was my duty, and I felt like nobody could do it better than I could because it was just my years and years and years of learning how to perfect blowouts. You know, plus the fact that, you know, now, I had these other partners, and people could help me really bring this thing to life. It’s just like it felt so meant to be.

“I really felt, like, it was my duty, and I felt like nobody could do it better than I could because it was just my years and years and years of learning… It’s just like it felt so meant to be.” Alli Webb

And so I got kind of that bug to get out there and do something again. And, you know, Drybar, the first location was very…it was in the middle of a recession and it was very… we were very unsure if it was going to work. And I remember my brother saying to me, "Why don’t you want to do cuts and color, too, where there’s more money?" And I was, like, "I just don’t want to. I’ve made…what I love about this industry is the blow-drying." And I also, by the way, didn’t know if there would be enough hairstylists out there who would also like the blow-drying part of doing hair only.

And so everything about it was a big risk, but there was just something in my gut that was telling me, "You know, I think women will spend the money on this." It will become this affordable luxury for women who at that point didn’t have access to celebrity hairstylists that would come over to their house and not charge them…would charge them upwards of $200, $300. You know, it was like we made the price point right. The experience and the décor, and the pace, and the customer service, and all that stuff, you know, really amazing. And plus you’re getting like this red-carpet ready hair. I just thought, "Surely, women would like this, and maybe we can make one store work."


Starting Projects that Grow and Give Back

Jessica: What’s interesting is you’re saying you were antsy to do something for yourself. But, ultimately, I think really you were wanting to do something for others. Because I think your fulfillment as a mom came from you were poring into these little people and there’s so much fulfillment from that because ultimately, hairstyling is about helping other women.

“What’s interesting is you’re saying you were antsy to do something for yourself. But, ultimately, I think really you were wanting to do something for others.” Jessica Honegger

Alli: Oh, 100 percent. I mean, you know, when I say I wanted to do something for myself, it’s, like, I had…back to your question about being driven, and I think I felt this desire to start this business because I felt it was something that was really missing, and that women, or at least women in LA, need it. And so that was the reason.

But yeah, I mean, I think that I did also kind of think it was a little bit of a vain business, and at least when you get your hair cut and colored, like, there’s an actual change, and there’s something actually changes. And I kind of felt like, with just blowouts, is this an incredibly vain business or…? I didn’t really think about it that much. I just…

Jessica: You were passionate about that aspect of it as much.

Alli: Well, I was. You know, I definitely was. I was so passionate about hair and blowouts, and the reaction that I was getting from women in my mobile business and how much they responded. And a lot of them were referrals and they had never even had a blowout before. And so it was definitely this passion.

But I didn’t realize the impact it would have when we first opened, and I saw from the get-go how women would react, obviously, in a much larger scale because I was just doing a handful of women a day, where now we’re doing like 80 to 100 people a day. And we would see it over and over again how the change and the transition these women experienced.

I remember and I know it sounds so silly, but I remember when we first open and I would not even recognize women after they were done with their blowout. I was like, "Where did she come from?" Because it was so hectic and crazy, and I was like, "Where did that women come from?" because we’re seeing so many people.

But it’s because most women walk into Drybar with their hair in a bun or hat on, very serious, all business and then when they’re done, there’s this visible pep in their step. They’re looking at themselves in every mirror and there’s this confidence that just exudes from them that, once I realized that, I was like, we are really onto something. We have captured lightning in a bottle here. I didn’t see that as much.

I just thought, I am a girl who has curly hair and always wanted to blowout and I have enough other friends who also want a blowout. This is a great idea for business. I don’t think I realized quite the impact that it would have on women and how women respond to it, and how women don’t go to a board meeting without a blowout or an important interview, or a date, or whatever it is.

Jessica: Well, it’s so powerful. I remember when we work in countries around the world. And in East Africa in particular, we work with this group of women and when I first started working with them, I remember their hair was cut really, really close to their heads and they were a little bit…you know, they had just started. They were just getting a really dignified job for the first time in their lives, and then I remember visiting them a year later and they had weaves. Some of them had like purple braids and it was like they had transformed because now their job had enabled them to get their hair done.

I mean, it’s just there’s something about our hair that brings dignity and confidence, and it is powerful. And then, of course, what happens in the salon chair. I mean, that’s a whole other thing, you know, those conversations. So, I love how it ended at being this thing that really does bring empowerment and beauty to women. So, take us back now to how do you transition from straight at home to Drybar because that is a big leap?

“There’s something about our hair that brings dignity and confidence, and it is powerful. And then, of course, what happens in the salon chair. I mean, that’s a whole other thing, you know, those conversations. So, I love how it ended at being this thing that really does bring empowerment and beauty to women.” Jessica Honegger


Getting Started by Asking for Help

Alli: Well, that process happened slowly, and it was a lot of figuring out all other stuff we didn’t know. My brother put in the lion share of the money which is lucky. You know, now I know because we raised so much money from institutions money. But Michael did put in the majority of the money and we put in what we had which was very little, but that’s when I learned the term sweat equity which, you know, where I was like, "I like sweat equity." It was basically I owned half the business and my brother owned half the business. I was running it and I was in the weeds in the day-to-day operation, then he put up the majority of the money and at the time, Michael was also running another company. And then Cameron, my husband, was working in advertising.

And so, he was the one who like really created the brand and the brand identity based on the vision I had for this which was to be like a bar. I wanted it to be like bright and sunny, but I wanted it to be very clean. So, between his creative and branding expertise, and my brother understanding business and putting the spreadsheets together and I was on the phone with the cosmetology board I feel like every second of my life, during that time, trying to figure out what I needed and what I didn’t need and getting towels and getting stylists and figuring it all out. That was what was happening between Straight at Home and Drybar ultimately opening.

And I tell people this a lot because I speak a lot and talk a lot about it to other entrepreneurs. And it’s just like you just have to start and you just have to go, and you just have to start making the phone calls and making lists and figuring out all the things that you need. And in figuring out what things you’re good at, what things your partners are good at and how much money you need. I mean, it’s just like, there’s a gajillion things that you have to do in those…well, there’s always a gajillion things that you have to do. But in those early days, you’re just doing anything and you just have to, you plow through it and figure out where you need the help. And so, I think, that was what we did.

“You just have to start and you just have to go, and you just have to start making the phone calls and making lists and figuring out all the things that you need. And in figuring out what things you’re good at, what things your partners are good at… you’re just doing anything and you just have to, you plow through it and figure out where you need the help.” Alli Webb

We asked a lot of people for help. We asked a lot of people for advice, friends, family, whoever would talk to us to get to where we needed to go. I think that’s a really important message because I talked to a lot of entrepreneurs who are in the throes of it or trying to start a business in their…they just feel like there’s too much they don’t know. So, they’re like, "I don’t know if I could do it."

Jessica: And they also are too afraid to reach out and ask for help.

Alli: Right, yeah. I mean…

Jessica: I find that a lot of people don’t actually ask for help when they need to.

Alli: Yep, it’s true, and I always tell people, like, you’d be really surprised how many people you can leverage in your own personal network. It’s like you have a friend who is a lawyer who will just give you some free advice. You know, there’s always somebody, I believe, willing to help, and I help people, especially my friends, as often as I can.


Rethinking Risk

Jessica: Absolutely. OK, so, I want to know, did you…at what point did you feel risk or did you? It’s funny. I heard on some NPR episode years ago, and they did the study, and they’re like, "Entrepreneurs actually aren’t any more risk-takers than anyone else. They just believe so 100% in their success that it doesn’t really feel like risk to them," and it sounds like you kind of were like, this is going to take, like, this is a hole in the market. Did you feel risk partnering with your brother as far as like, “Oh my gosh, now I’ve got money on the line, now I’ve got to really monetize this”?

Alli: Yeah. I mean, I think there was fear. It’s so funny that talking about it now because we’re almost nine years in, and knock on wood, so successful and proved the model, and all of those things. But when I think back to days before we opened the first shop in Brentwood and how much anxiety I had over it, and I was like doing the math in my head thinking like, "If we can just get five women an hour." I was doing the math to try to figure out what it would look like to be successful. 

I think that there’s always going to be fear and anxiety and worry about the risk. But kind of true to what you said, I think the way I always felt about it was no one was going to die, and I’ve said it a million times. I always say this because this is how I felt. I felt like it would have really sucked. You know, my brother put a lot of money into this and it would have been such a shame if it didn’t work, but no one was going to die, and everyone would have picked themselves up and gotten other jobs, and we would have moved on with our lives.

And I think that that’s the difference, maybe. I think a lot of people are scared of that. What if it doesn’t work? If it doesn’t work, I’m going to be out all this money. I wasted all this time and blah, blah, blah. I’m like, "But, really, who cares?" It’s like, yeah, you fall down in life, and you get back up. And I think that’s what I felt like we were all really smart. In the early days, I was really the only one putting my time on the line. Cameron was still working at his advertising agency. Michael was still managing another business. It wasn’t until about a year so that they came into the company like full throttle. I mean, they were, of course, really helping me. 

So, I think you do have to be slightly risk-adverse and not be so paralyzed by your fear. And if you are, you just can’t do it because you can’t focus in that kind of environment, and I just wasn’t. I had fear, I had an anxiety, but I wasn’t paralyzed by that.

“I think you do have to be slightly risk-adverse and not be so paralyzed by your fear. And if you are, you just can’t do it because you can’t focus in that kind of environment, and I just wasn’t. I had fear, I had an anxiety, but I wasn’t paralyzed by that.” Alli Webb

Jessica: Right. It’s called The Going Scared Podcast. So, we’re all about just walking through your fear because that’s how it’s done. People want this magic formula and it’s like you just get up and you go. That’s the trick.

“People want this magic formula and it’s like you just get up and you go. That’s the trick.” Jessica Honegger

Alli: And I think, it’s like, it has to be hard sometimes.

Jessica: It is, yeah.

Alli: And then I’ve always felt like that. When things are hard, I think it means like there’s such a promise of things getting better. If things are bad, they usually are only going to get better, and to me, that’s always kind of kept me going. Like, I might feel bad now or things are hard right now, but I know that there’s kind of a light at the end of the tunnel, and I think I’m just a fairly optimistic person and that’s how my mother was. And so, I think I just inherited that, but I think a lot of people have a hard time with that, but that’s just kind of how I see the world, I guess.


Letting Go of Perfection

Jessica: So, I wanted to ask you about that. Let’s talk about hard because I feel like founders get asked a lot about our origin stories, but then people don’t often hear about the one million choices after that original start that shape and steward the brand. So, can you describe a season over the last few years in particular that have required perseverance and kind of saying, I’m not going to quit?

Alli: Well, I mean, as great as the growth of Drybar has been, a hundred percent didn’t come without a lot of pain points, and especially trying to figure it all out in those early years and having a really good problem on our hands with being so busy and having such kind of immediate success. It just kind of like got to the point where we were like, this is so big and we don’t totally know how to do this because the vision of the company and what I wanted to do, which I’ve talked about, is give great hair to women, as many women as we could, and create an amazing experience in Drybar, great customer service, the TVs, all the things. 

But then it’s like, all of a sudden, we turned around and we had 300 employees, and then we had 500 employees. And it’s like, that’s a whole other business. We had to start a call center because the call volume is so incredibly high. We couldn’t answer the phones in the shops. There was a lot of things that operationally where we’re like, "Uh-oh, we don’t know how to do any of that." And so, that in and of itself became just kind of a challenge that we had to deal with that we didn’t know how to do, and I think we’re entrepreneurs.

I had this vision of what I wanted, but then carrying that out and making sure that people are getting paid, and people are happy, and all of those things. That requires a lot of help. And so, that’s when we started to bring in more experienced, seasoned executives, and that was kind of hard for me because I really had to get comfortable, and this is, I’m sure, something a lot of founders talk about. 

I had to get comfortable with giving up a little bit of control and decision-making because I had to bring in other people and I had ultimately let them make decisions. And that was a very long transition that took me a long time to get comfortable with. It was definitely challenging to take on that like next level of, well, you aren’t going to make every decision, but it was a slow build, and ultimately, we ended up bringing in a professional CEO, and my brother was CEO before that.

“I had to get comfortable with giving up a little bit of control and decision-making because I had to bring in other people and I had ultimately let them make decisions. And that was a very long transition that took me a long time to get comfortable with.” Alli Webb

It definitely happened slowly, and I felt like way evolved on it now, but those were like some really tough years for me, letting go to a certain extent, and I really struggled with that. It was a lot of long conversations and a lot of…for me, like learning and growing how to…learning how to give feedback and how to not lose my cool and how to communicate with people in the right way and all of those things that you have to learn when you’re running a business. 

So, that was a really tough time and I would say that was probably, maybe from year like three to…what are in, like, almost year eight now. I’d say last like three or four years, and I think I’ve only recently come out of that and feel like it really let the teams kind of do their thing and have a much more peripheral view of what’s happening. There are some things that I won’t let go, but I’d still weigh in on a lot of things, but let the team really fly and that’s really empowering. And that’s been something that I felt really proud of that I’ve worked really hard to get to.

Jessica: Yeah, that’s incredible. I mean, honestly, that is one of my little selfish reasons that I’m like, I want to have Alli mentor me on my podcast because I did want to ask you about role. We finally have our executive team as fully set. We’re at about 20 million, but we really have dreams and desires to scale pretty quickly over the next couple of years, and as the founder, I am in that pivotal place right now of what is my role? Like, why does my role need to shift now? 

And I’m curious, how do you decide that where you’re most needed in the business and then how do you measure, if you’re spending your time in the right places because not…founders, not everyone writes a book or starts a podcast or speaks, and you seem to really enjoy all of those things. And so, how do you, sort of, evaluate where to spend your time now as your role has shifted?

Alli: Well, I think that, you know, it is determining kind of your highest and best use. And I think that that has changed and transitioned a little bit here and there. That has definitely changed for me. Again, it was a lot of really heartfelt conversations with my brother and our CEO John, who I just absolutely adore. It definitely kind of happened in phases, but I think when I say highest and best use, I think it really is about figuring out what I actually really like to do and what I’m actually really good at, which may not be one in the same for everybody. But for me, it’s like I did…there’s a couple of, kind of, sacred cows, right? 

There’s product development. We have a massive team on product development and who do the majority of the work, but there will never be, as far as I can see, there will never be a product that gets released into the world that I didn’t personally sign off on and part of the development process. I mean, there’s a lot of ways that we evaluate products, and we send them out into the field, and we do lots of different testing’s in lots of different ways, not on animals or anything, just in case anybody is listening. So, there’s a lot of different ways, but that’s still a very sacred thing to me because I obviously have such a deep sense of hair and it’s where I come from.

So, there’s things like that and I’m obviously the face of the brand and I do all the press and I do all of that kind of stuff. But there are definitely instances now where we have some of our top trainers go in and do certain things when it comes to press and things like that which is also involved to kind of say, obviously I still do the majority of it and the big stuff. And I do all, not all, but I do the majority of our hair training videos and things like that. The things that, again, I’m good at.

I really understand hair from a fundamental level. I understand how to style hair. I mean, I feel like nobody can do it the way I can do it and I felt very proud of that, and that’s something that I can speak really well on behalf of the brand. I’ve been doing it for nine years. So, those are the things that we’ve all kind of isolated out.

Jessica: And was there a point when you were going through this transition conversations where you, kind of, how to own that? Like, "Well, you know what? I am good at this. I am a specialist in this." Because I know you’re trying to think where can I be replicated and where can I not be replicated?

Alli: Yeah, 100 percent. I still obviously weigh in a lot on PR and marketing. We have the CMO and we have a whole team of marketing people. A lot of them have been with us for a long time and they know, kind of, how I like and want things. But you also need to rub there. You need somebody pushing back on things that we’ve been doing for a long time saying, "How about we try this?"

And I think that for the most part, it’s good. And I remember even having a conversation with my brother not very long ago when I was very frustrated at something that was going on, that one of our teams was doing. His response to it was like, "You’ve got to just let them do it and if it fails, it fails and then they’ll learn." 

And I was like, "You know what? You’re right," because just like we made, of course we’ve made mistakes and then you learn from them. I mean, it was like we have to enable our teams and the people we’ve put in place to do that too and I think that was very enlightening for me because I was like, "OK, the world is not going to end. The business is not going to fail."

Jessica: No one’s going to die.

Alli: Yeah, and it’s funny because I really used to feel that way. It felt like, oh, my god. If we didn’t do X, Y, and Z, it was all over. The business was going to fold. I mean, I really was like that dramatic about it in the early years. It’s like when I would walk in the store and it wasn’t up to par and up to standard for me, I would lose my mind and I would be so mad, and I would be so frustrated and like, "Why can’t we get this right? Why are we doing this?" 

Which I learned as like…first, I learned that there’s no such thing as perfect and also, I learned that you’ve got to coach people and you got to get them to the right place and you make improvements. It’s like, you just can’t do it all the time. This is the very evolved me talking, but it was really hard when I was in the throes of it and you have to just make some peace, I think, with the fact that not everything is always going to be perfect exactly how you wanted. You pick your battles and all of that.


Having the Power to Create Impact

Jessica: Yeah. No, what does that look like from a process perspective though because you still have a say, you still have these areas of the business where…I mean, you’re obviously the brand ambassador and do you enjoy that? Is that a dumb question? I mean, you started a podcast, you wrote a book.

Alli: No, I love it.

Jessica: So, you love that part which I think is a secret sauce too because I think there’s a lot of founders that are like… But, I mean, really, I think it adds a lot to the brand.

Alli: No, I mean besides my children, there’s nothing in the world I’m prouder of than starting Drybar. I mean, I think it’s like I still pinch myself. I can’t even describe how proud I feel that this little idea of mine has turned into what it has.

Jessica: Oh, my gosh. It’s incredible and I meet people all the time.

Alli: Incredibly proud and I feel like it’s like, it put me on the map. It gave me a voice. It gave me so much opportunity. The things I get to do now and the person I get to be. I mean, the fact that…I mean this with so much humility. I mean, the fact that people want me to come and speak at events and talk about my experience. I still turn around and I’m like, "Me?" Because I feel like I was such like an underdog. 

I didn’t go to college. I don’t have a formal education. It was just such a scrappy kid and it’s funny. It’s really funny to me how much I’ve learned and how far I’ve come. And yeah, so, none of that would have happen without Drybar and also without my incredible partners and the incredible people around us. And in terms of processes like you ask, I mean, I think that that is something that when you have to bring in really great people who are…

Jessica: Who know how to answer you because that’s what I’m curious about.

Alli: Yeah. They understand working in the founder-led organization and of course it may have evolved in the last couple of years for me, but with my brother and with me. It’s like, there are people and I have found this because we employ a lot of people who are much more comfortable in a very corporate environment. And there’s just not the same kind of emotion I guess that there is in a founder-led organization.

Jessica: No, and family too because you’re working with your family, founder and family.

Alli: Exactly. And so, not everybody, again we have found out, is cut out to be in that kind of organization. Like when we brought in John, who’s our CEO, he had worked in a founder led organizations. He did understand the dynamic of that and how and this was like a family run business and you have to…you got to have a thick skin and be comfortable being in that environment.

I don’t know what it’s like to be in that as an outsider because it’s my business, but John really did and he really understood it. And I think all of our executive leaders really understand it. I don’t think they all always have, but I think we happen to have an exceptional team in place right now.

And so, I think that is part of maybe the process of figuring that out because you can very easily come across people, executives who might be amazing, but they’re just like…it’s a different dynamic when you’re working for like an impassioned founder who’s going to throw a monkey wrench in your plans all the time. You have to be OK with that, really OK with that. And if you’re not, it’s just not the right place for you because…

Jessica: And not even just OK with it, but also acknowledging that that is part of the success.

Alli: Exactly, that’s very true.

Jessica: So, I run in to people all the time who you have inspired. I was at a hairstylist the other day and she was like, "Oh, my god. You’re getting to talk to Alli. She has completely changed my life." So, when you hear these stories, what’s one story or couple stories, or sort of a theme that sticks out to you that you were just so proud of, that you’re like, “Wow, I’ve really helped change the world in a way”?

Alli: Yeah. I mean, it’s such a trip. I mean, I can’t believe how many notes I get like that, like what you just said. I mean, how so many…whether they’re a budding hairstylist or just…you know, I just got a note from my girl who said she was a nurse practitioner, but she really wanted to go to cosmetology school and then read about and my story and like was going to do it. 

You know, I get notes like that a lot or just someone in a completely different industry who just kind of, you know, had listened to my, How I built This podcast or my podcast Raising the Bar, whatever. They listen or know the story. They felt like, again, if she did it, I can do it kind of mentality. And it is something I hear, and I get via DM and email all the time. Yes, I mean, it’s really mind-blowing to me and…I mean, obviously, it feels so good and so rewarding that I inspire people or what I’ve done inspires people. Actually, what we’ve done because I certainly did not do it alone, not by a longshot.

Jessica: Well, it seems like you’ve created a really special culture, too. I mean, I’ve just heard the culture of your employees and your stylists is really lifegiving.

Alli: Yeah. I mean, we really have tried to create an environment where stylists feel like they’re part of something and they’re well-taken care of. I mean, I don’t think that Drybar is for everybody. It’s a very labor-intensive job. And it just is and it’s a lot, and you’re always busy which is to me, I thrive in that kind of environment, but then we have founder stylist who prefer to be in a cut-and-color salon where they can take 20-minute breaks between clients and things. It’s just that’s not how we are, and I think that there’s, to your point, we employ almost 3,500 stylists and I think they really just love to be a part of this brand, of this movement, this thing that we created, and they’re proud to be part of Drybar.

Yeah, I mean, there’s nothing better than that. So, we’re also proud of that, and we do a lot to nurture that. We have these heart and soul cards that have our 10 core values which basically are like, "We are family," and, like, "Life is too short to work someplace lame," and "Be yourself," and all of these things. And then, we have these cards that in the stores where stylists can give them to each other and pin them up on a wall and, kind of, say something great that they thought another stylist did or…and you know, it’s this kind of gratitude that we give back and things like that. 

“We employ almost 3,500 stylists and I think they really just love to be a part of this brand, of this movement, this thing that we created, and they’re proud to be part of Drybar. Yeah, I mean, there’s nothing better than that. So, we’re also proud of that, and we do a lot to nurture that.” Alli Webb

And then just silly things, like, always making sure there are snacks for our stylists and buying them lunch sometimes. Whatever it is. I mean, there’s definitely this camaraderie at Drybar and the fact that there’s a lot of flexibility. They can work for us and work for a full-service salon. They can leave us and go work for a full-service salon and then come back to us if they’re slow at their salon. So, there’s an incredible amount of flexibility, and I think it really does feel like a home.


Confidence in Being Willing to Learn

Jessica: OK. So, let’s talk a sec about confidence. You know, when you think back to the anxiety-ridden Alli, the night before the Brentwood store opens and the person you are now, what are some things along the way that have helped you to build your confidence legs?

Alli: Yeah. I mean, I definitely wasn’t super confident, not the way I am now, when we first started, and I think…first and foremost, seeing this little idea take off. I mean, that was obviously as you can imagine, was a massive confidence builder and seeing the way women were reacting to what we are doing was like just unbelievable. And I think that instilled a ton of confidence in me. 

And you know, and then seeing how the rest of the world and the press, and the stylists and all of that responded to this idea. It was kind of like, a moment for me where I was like, "Wow. That’s pretty amazing. Who knew?" And so, I think it just, kind of, slowly but surely started just instilling a lot more confidence in me. And then it was like just the learning process of growing this business and learning from other people.

Learning from a lot of the executives I’ve talked about and learning how to navigate a lot of the things that I didn’t know in terms, and then raising money. There’s just like thing after thing that I’ve learned over the last nine years that have really, I think, rounded me out as a person and I felt so much smarter and more, just well-versed in the world, and I think that that, kind of, happens slowly over time. It’s like the old cliché, like, "Knowledge is power." I mean, I do feel like that. 

I feel like when you’re more knowledgeable about, like, what you’re doing, how you’re growing as a person, it does make you feel like a lot more confident and powerful. And the ability, you feel like you can conquer the world. So, I think that happened for me slowly over time and I think there’s something to do with age too. When we started Drybar I was around like 35, 36. I’ve grown a lot as a person and you just when you hit your 40s, you start to feel like, "I got this."

Jessica: All right. So, you definitely got some behind the scenes. We’ve wrapped up our Imperfect Courage series and now we’re really diving into what my role looks like at Noonday collection. So, I took this as an opportunity to ask her some questions that I really appreciated. I hope you appreciated them too. 

Thanks so much for tuning in today. Make sure you go and leave a review on iTunes. I know that I say this on a lot of my episodes, but this is how people find Going Scared. So, if this podcast has meant anything to you which so many of you have told me it does, just hop on real quick and leave a review.

I love what one reviewer said. She said, "Listening to Jessica is like talking with a girlfriend over a cup of coffee. She shares her own stories in a vulnerable way while celebrating other women every chance she gets. The biggest thing that I’ve learned from her is that another woman’s success does not diminish my own."

Thanks for tuning in today. Our wonderful music is by my good friend, Ellie Holcomb. Going Scared is produced by Eddie Kaufholz and I’m Jessica Honegger. Until next time, let’s take each other by the hand and keep Going Scared.